Synergistic fungicidal composition comprising a compound analogous to strobilurin

ABSTRACT

Synergistic fungicidal composition comprising a compound analogous to strobilurin of formula (I): ##STR1## in which: A is the nitrogen atom or the --CH group, 
     B is the --OCH 2  -- or --CH 2  O-- or CH(CH 3 )--O--N═CH-- or --CH═N--O--CH(CH 3 )-- group or the group ##STR2##  R 1  is an alkyl group containing 1 to 4 carbon atoms, R 2  is --OCH 3  or --NHCH 3 , 
     X is a halogen atom, the cyano group or an alkyl or haloalkyl group containing 1 to 4 carbon atoms, 
     n is equal to 1 or 2, with, when n is equal to 2, the possibility of having different X groups, 
     and at least one fungicidal compound B, and 
     a process for the curative or preventive control of phytopathogenic fungi using the composition.

This application is a divisional of application Ser. No. 08/983,625,filed May 13, 1998, now U.S. Pat. No. 6,015,802, incorporated byreference herein in its entirety and relied upon, which is the U.S.national phase of International Application No. PCT/FR96/01155, filedJul. 23, 1996.

The subject of the present invention is a synergistic fungicidalcomposition comprising a compound analogous to strobilurin and a processwhich makes use of the said composition and which is intended for thecurative or preventive protection of crops against fungal attacks.

Compounds analogous to strobilurin with a fungicidal effect are known,in particular from European Patent Application EP 253213 or 398692 orfrom international Application WO 9208703, which make it possible toprevent the growth and the development of phytopathogenic fungi capableof attacking crops.

However, it is always desirable to improve the spectrum of activity andthe effectiveness of such compounds with a fungicidal effect or toreinforce them by combining them with other molecules in order to obtaina more effective product (combination with a systemic fungicide, thesefungicides instead being molecules of "contact" type) or alternativelyto prevent the appearance of fungal strains which are resistant to thesenew fungicides.

It is also highly desirable to have available fungicidal products whichenjoy an improved persistence of effect, likely to space out in time thenumber of plant-protection treatments necessary for satisfactory controlof the parasites.

It is, in any event, particularly advantageous to be able to decreasethe amount of chemicals distributed in the environment, while ensuringhigh-performance protection of crops against fungal attacks.

It has now been found that one (or a number) of the above objects couldbe achieved by virtue of the fungicidal composition according to thepresent invention.

The present invention accordingly provides a synergistic fungicidalcomposition comprising at least one compound A of formula (I): ##STR3##in which: A is the nitrogen atom or the --CH group,

B is the --OCH₂ -- or --CH₂ O-- or --CH(CH₃)--O--N═CH-- or--CH═N--O--CH(CH₃)-- group or the group ##STR4## R₁ is an alkyl groupcontaining 1 to 4 carbon atoms, preferably the methyl group,

R₂ is --OCH₃ or --NHCH₃,

X is a halogen atom, the cyano group or an alkyl or haloalkyl groupcontaining 1 to 4 carbon atoms, preferably the methyl or trifluoromethylgroup,

n is equal to 1 or 2, with, when n is equal to 2, the possibility ofhaving different X groups,

and at least one fungicidal compound B chosen from the group consistingof phosphorous acid and derivatives thereof, for example metalphosphites, such as fosetyl-Al, and alkali metal or alkaline-earth metalsalts of phosphorous acid. The compositions will generally contain onecompound A.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is an isobole plot for ICIA 5504, i.e. methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,and fosetyl-Al in Chardonnay vine cuttings against Plasmopara viticola(grape downey mildew); and

FIG. 2 is an isobole plot for SSF-129, i.e. N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide, andfosetyl-Al in Chardonnay vine cuttings against Plasmopara viticola.

The fungicidal composition according to the invention advantageouslycomprises the components A and B in an A/B ratio by weight of from 0.004to 1, preferably from 0.0125 to 0.4.

It is clearly understood that the said fungicidal composition cancontain a single compound B or more than one such compound, for example1, 2 or 3 compounds B, according to the use for which the combination isintended. The composition may also comprise more than one compound A.

Preference is given to the fungicidal composition according to theinvention in which the compound A is methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl (E)-methoxyimino[α-(o-tolyloxy )-o-tolyl]acetate orN-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide.

Preference is further given, among the more especially preferredmeanings of the compound B defined above, to fosetyl-Al. In an entirelyunexpected way, the combination according to the invention thensignificantly improves the effect of the active materials takenseparately with respect to a number of fungi which are particularlyharmful to crops, for example in particular grapes or the Solanaceae.This improvement is reflected in particular by a decrease in the dosesof each of the constituents, which is particularly advantageous for theuser and the environment. The fungicidal product thus exhibitssynergistic properties attested by application of the Tammes method,"Isoboles, a graphic representation of synergism in pesticides",Netherlands Journal of Plant Pathology, 70(1964), p. 73-80.

Preferably, when the component B is fosetyl-Al, the A/B ratio is from0.01 to 1, preferably from 0.033 to 0.4, for all the crops envisaged.

In the particular case of lawns, the A/B ratio will be from 0.004 to0.4, preferably from 0.0125 to 0.1.

The structures corresponding to the common names of the fungicidalactive materials which appear in the definition of B are shown in atleast one of the following 2 works:

"The Pesticide Manual", edited by Clive Tomlin and published by TheBritish Crop Protection Council, 10^(th) edition;

l'Index phytosanitaire [Plant-protection index] 1994, published byl'Association de Coordination Technique Agricole [Agricultural TechnicalCoordination Association], 30^(th) edition.

As regards the compounds A analogous to strobilurin, methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate(or ICIA5504) is described in International Application WO 9208703;methyl (E)-methoxyimino[α-(o-tolyloxy)-o-tolyl]acetate (or BAS490F) isdescribed in European Patent Application EP 253213; andN-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide(or SSF-129) is described in European Patent Application EP 398692.Moreover, ICIA5504 and BAS490F are listed in the abovementioned work"The Pesticide Manual".

The fungicidal composition according to the invention comprises, asactive material, at least one compound A and at least one compound B asa mixture with solid or liquid vehicles which are acceptable inagriculture and/or surface-active agents which are also acceptable inagriculture. In particular, the inert and conventional vehicles and theconventional surface-active agents can be used. These compositions covernot only compositions which are ready to be applied to the crop to betreated by means of a suitable device, such as a spray device, but alsocommercial concentrated compositions which have to be diluted beforeapplication to the crop. The combination of at least one compound A withat least one compound B is denoted as active material.

These compositions can also contain any kind of other ingredients suchas, for example, protective colloids, adhesives, thickening agents,thixotropic agents, penetrating agents, stabilizing agents, sequesteringagents and the like. More generally, the compounds A and B can becombined with all the solid or liquid additives corresponding to theconventional formulating techniques.

Generally, the compositions according to the invention usually containfrom 0.05 to 95% (by weight) of active material, one or more solid orliquid vehicles and, optionally, one or more surface-active agents.

In the present account, the term "vehicle" denotes a natural orsynthetic, organic or inorganic material with which the active materialis combined to facilitate its application on the aerial parts of theplant. This vehicle is thus generally inert and it must be acceptable inagriculture, especially on the treated plant. The vehicle can be solid(clays, natural or synthetic silicates, silica, resins, waxes, solidfertilizers and the like) or liquid (water, alcohols, especiallybutanol, and the like).

The surface-active agent can be an emulsifying, dispersing or wettingagent of ionic or nonionic type or a mixture of such surface-activeagents. There may be mentioned, for example, salts of polyacrylic acids,salts of lignosulphonic acids, salts of phenolsulphonic ornaphthalenesulphonic acids, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, substituted phenols,(especially alkylphenols or arylphenols), salts of esters ofsulphosuccinic acids, taurine derivatives (especially alkyltaurates),phosphoric esters of polyoxyethylenated phenols or alcohols, esters offatty acids and of polyols, and the derivatives of the above compoundscontaining sulphate, sulphonate and phosphate functional groups. Thepresence of at least one surface-active agent is generally indispensablewhen the active material and/or the inert vehicle is/are not soluble inwater and the carrier agent for application is water.

The compositions for agricultural use according to the invention canthus contain the active material within very wide limits, ranging from0.05% to 95% (by weight). Their surface-active agent content isadvantageously of between 5% and 40% by weight. Unless otherwisespecified percentages in this specification, including the accompanyingclaims, are by weight.

These compositions according to the invention are themselves in fairlydiverse, solid or liquid forms.

There may be mentioned, as forms of solid compositions, the powders fordusting (with an active material content which can range up to 100%) andthe granules, especially those obtained by extrusion, by compacting, byimpregnation of a granulated support, or by granulation from a powder(the active material content in these granules being between 0.5 and 80%for the latter cases), the tablets or effervescent tablets.

The fungicidal composition according to the invention can also be usedin the form of powders for dusting; it in also possible to use acomposition comprising 50 g of active material and 950 g of talc; it isalso possible to use a composition comprising 20 g of active material,10 g of finely divided silica and 970 g of talc; these constituents aremixed and milled and the mixture is applied by dusting.

There may be mentioned, as forms of liquid compositions or thoseintended to constitute liquid compositions at the time of application,solutions, in particular water-soluble concentrates, emulsions,suspension concentrates, aerosols, wettable powders (or powder to besprayed), pastes or gels.

The suspension concentrates, which can be applied by spraying, areprepared so as to obtain a stable fluid product which does not settleout and they generally contain from 10 to 75% of active material, from0.5 to 15% of surface-active agents, from 0.1 to 10% of thixotropicagents and from 0 to 10% of suitable additives, such as antifoamingagents, corrosion inhibitors, stabilizing agents, penetrating agents andadhesives and, as vehicle, water or an organic liquid in which theactive material is insoluble or nearly insoluble: certain organic solidmaterials or inorganic salts can be dissolved in the vehicle to aid inpreventing sedimentation or as antigels for water.

A suspension concentrate composition in given here as an example:

    ______________________________________                                        SC Example 1:                                                                 ______________________________________                                        active material              500 g                                              polyethoxylated tristyrylphenyl phosphate   50 g                              polyethoxylated alkylphenol   50 g                                            sodium polycarboxylate   20 g                                                 ethylene glycol   50 g                                                        organopolysiloxane oil (antifoaming agent)    1 g                             polysaccharide   15 g                                                         water 316.5 g                                                               ______________________________________                                    

Wettable powders (or powder to be sprayed) are generally prepared sothat they contain 20 to 95% of active material, and they generallycontain, in addition to the solid vehicle, from 0 to 30% of a wettingagent, from 3 to 20% of a dispersing agent and, when this is necessary,from 0.1 to 10% of one or more stabilizing agents and/or otheradditives, such as penetrating agents, adhesives, or anticlumpingagents, dyes, and the like.

To obtain powders to be sprayed or wettable powders, the activematerials are intimately mixed, in suitable mixers, with the additionalsubstances and the mixture is milled with mills or other suitablegrinders. Powders to be sprayed are thereby obtained with advantageouswettability and suspensibility; they can be suspended in water at anydesired concentration and these suspensions can be used veryadvantageously in particular for application to plant leaves.

Pastes can be produced in place of wettable powders. The conditions andmodes of production and use of these pastes are similar to those ofwettable powders or powders to be sprayed.

Various wettable powder (or powder to be sprayed) compositions are givenhere as examples:

    ______________________________________                                        WP Example 1                                                                      active material             50%                                             ethoxylated fatty alcohol (wetting agent)  2.5%                               ethoxylated phenylethylphenol (dispersing agent)   5%                         chalk (inert vehicle) 42.5%                                                 WP Example 2:                                                                     active material             10%                                             C13 branched-type synthetic oxo alcohol, 0.75%                                ethoxylated with 8 to 10 molecules of                                         ethylene oxide (wetting agent)                                                neutral calcium lignosulphonate   12%                                         (dispersing agent)                                                            calcium carbonate (inert filler) qs for 100%                                WP Example 3:                                                                   This wettable powder contains the same ingredients as                         in the above example, in the proportions below:                                 active material             75%                                             wetting agent 1.50%                                                           dispersing agent   8%                                                         calcium carbonate (inert filler) qs for 100%                                WP Example 4:                                                                     active material             90%                                             ethoxylated fatty alcohol (wetting agent)   4%                                ethoxylated phenylethylphenol (dispersing agent)   6%                       WP Example 5:                                                                     active material             50%                                             mixture of anionic and nonionic surface-  2.5%                                active agents (wetting agent)                                                 sodium lignosulphonate (dispersing agent)   5%                                kaolin clay (inert vehicle) 42.5%                                           ______________________________________                                    

Aqueous dispersions and emulsions, for example the compositions obtainedby diluting a wettable powder or an emulsifiable concentrate accordingto the invention with water, are contained within the general scope ofthe present invention. Emulsions can be of the water-in-oil oroil-in-water type and they can have a thick consistency, like that of a"mayonnaise".

The fungicidal compositions according to the invention can be formulatedin the form of water-dispersible granules, which also come within thescope of the invention.

These dispersible granules, with a bulk density generally of betweenapproximately 0.3 and 0.6, have a particle size generally of betweenapproximately 150 and 2000 and preferably between 300 and 1500 microns.

The active material content of these granules is generally betweenapproximately 1% and 90%, and preferably between 25% and 90%.

The rest of the granule is essentially composed of a solid filler and,optionally, of surface-active adjuvants which conferwater-dispersibility properties on the granule. These granules can beessentially of two distinct types according to whether the filler heldis soluble or insoluble in water. When the filler is water-soluble, itcan be inorganic or, preferably, organic. Excellent results wereobtained with urea. In the case of an insoluble filler, the latter ispreferably inorganic, such as, for example, kaolin or bentonite. It inthen advantageously accompanied by surface-active agents (in aproportion of 2 to 20% by weight of the granule) of which more than halfconsists of, for example, at least one dispersing agent, essentiallyanionic, such as an alkali metal or alkaline-earth metalpolynaphthalenesulphonate or an alkali metal or alkaline-earth metallignosulphonate, the remainder consisting of nonionic or anionic wettingagents such as an alkali metal or alkaline-earth metalalkylnaphthalenesulphonate.

Moreover, although this is not indispensable, it in possible to addother adjuvants such an antifoaming agents.

The granule according to the invention can be prepared by mixing thenecessary ingredients and then granulating according to severaltechniques known per se (granulator, fluid bed, sprayer, extrusion, andthe like). The preparation generally finishes with a crushing followedby a sieving to the particle size chosen within the limits mentionedabove. Granules obtained as above and then impregnated with acomposition containing the active material can alternatively be used.

It is preferably obtained by extrusion, by carrying out the preparationas indicated in the examples below.

DG Example 1

Dispersible granules

90% by weight of active material and 10% of urea in the form of pearlsare mixed in a mixer. The mixture is then milled in a pin mill. A powderis obtained which is moistened with approximately 8% by weight of water.The moist powder is extruded in a perforated-roller extruder. A granularmaterial in obtained which in dried, and then crushed and sieved, so asto respectively keep only the granules with a size of between 150 and2000 microns.

DG Example 2

Dispersible granules

The following constituents are mixed in a mixer:

    ______________________________________                                        active material              75%                                                wetting agent (sodium alkylnaphthalene-sulphonate  2%                         dispersing agent (sodium polynaphthalene-sulphonate  8%                       water-insoluble inert filler (kaolin) 15%                                   ______________________________________                                    

This mixture is granulated on a fluid bed in the presence of water andthen dried, crushed and sieved so as to obtain granules with a size ofbetween 0.15 and 0.80 mm.

These granules can be used alone or in solution or dispersion in waterso as to obtain the required dose. They can also be used to preparecombinations with other active materials, especially fungicides, thelatter being in the form of wettable powders or granules or aqueoussuspensions.

As regards the compositions which are suitable for storage andtransportation, they more advantageously contain from 0.5 to 95% (byweight) of active material.

A further feature of the invention in a process for the curative orpreventive control of fungi which are phytopathogenic, for exampletowards crops or lawns, characterized in that an effective andnon-phytotoxic amount, in combination, of at least one compound A and atleast one compound B, for example in a fungicidal composition accordingto the invention is applied on the aerial parts of plants.

The fungi which are phytopathogenic towards crops which can be combattedby this process are in particular those:

from the Oomycetes group:

from the Phytophthora genus, such as Phytophthora infestans (downymildew of the Solanaceae, in particular of potatoes or tomatoes),Phytophthora citrophthora, Phytophthora capsici, Phytophthora cactorun,Phytophthora palmivora, Phytophthora cinnamoni, Phytophthora megaspermaor Phytophthora parasitica,

from the Peronosporaceae family, in particular Plasmopara viticola(grape downy mildew), Plasmopara halstedei (sunflower downy mildew),Pseudoperonospora sp (in particular downy mildew of cucurbits and ofhops), Bremia lactucae (lettuce downy mildew) or Peronospora tabacinae(tobacco downy mildew),

from the Adelomycetes group:

from the Alternaria genus, for example Alternaria solani (alternariadisease of the Solanaceae and in particular of tomatoes and potatoes),

from the Guignardia genus, in particular Guignardia bidwellii (black rotof grapes),

from the Oidiums group, for example grape powdery mildew (Uncinulanecator); powdery mildew of legumes, for example Erysiphe polygoni(powdery mildew of crucifers); Leveillula taurica, Erysiphecichoracearum, Sphaerotheca fuligena; (powdery mildew of cucurbits, ofcomposites or of tomatoes); Erysiphe communis (beet and cabbage powderymildew); Erysiphe pisi (pea or lucerne powdery mildew); Erysiphepolyphaga (bean and cucumber powdery mildew); Erysiphe umbelliferarum(powdery mildew of the Umbelliferae, in particular of carrots);Sphaerotheca humuli (hop powdery mildew); or Erysiphe graminis (powderymildew of cereals),

from the Septoria genus, for example Septoria nodorum or Septoriatritici (septoria disease of cereals);

from the Basidiomycetes group:

from the Puccinia genus, for example Puccinia recondita or striiformis(wheat rusts).

A classification made no longer by targeted fungi but by target cropscan be illustrated as below:

grapes: powdery mildew (Uncinula necator), downy mildew (Plasmoparaviticola), excoriosis (Phomopsis viticola) and black rot (Guignardiabidwellii),

Solanaceae: downy mildew (Phytophthora infestans), alternaria disease(Altenaria solani) and rot (Botrytis cinerea),

vegetable crops: downy mildews (Peronospora sp., Bremia lactucae,Pseudoperonospora sp. or alternaria disease (Alternaria sp.),sclerotinia disease (Sclerotinia sp.), rot (Botrytis cinerea) or powderymildew (Erysiphe sp. or Sphaerotheca fuliginea),

arboriculture: scab (Venturia inaequalis), powdery mildew (Podosphaeraleucotricha) and monilia disease (Monilia fructigena),

citrus fruits: scab (Elsinoe fawcetti), melanose (Phomopsis citri) anddiseases due to Phytophthora sp., bananas: cercospora disease(Mycosphaerella figiensis),

lawns: rust, powdery mildew, helminthosporium disease or soil diseases(Microdochium nivale, Pythium sp., Rhizoctonia solani, and the like).

The fungicidal combination which is the subject of the invention inapplied by means of various treatment processes, such as:

spraying the liquid comprising the said composition on the aerial partsof the crops to be treated,

dusting, the incorporation of granules or of powders into the soil,sprinkling, injecting into trees or painting.

The spraying of a liquid on the aerial parts of the crops to be treatedis the preferred treatment process.

"Effective and non-phytotoxic amount" is understood to mean an amount ofcomposition according to the invention which is sufficient to makepossible control or destruction of the fungi present or capable ofappearing on the crops and which does not result in any substantialphytotoxicity symptoms respect to the said crops. Such an amount iscapable of varying within wide limits depending on the fungi to becontrolled, the type of crop, the weather conditions and the compoundsincluded in the fungicidal composition according to the invention. Thisamount can be determined by systematic tests in the field, within thescope of the person skilled in the art.

The use doses during the implementation of the process according to theinvention will then generally be:

on grapes, vegetable crops, Solanaceae, bananas, arboriculture or citrusfruits:

500 to 5000 g of compound B, eg fosetyl-Al+50 to 500 g/ha of compound Aand more precisely 1000 to 3000 g+100 to 400 g/ha, i.e. a total dose ofcomposition according to the invention of from 550 to 5500 g/ha,preferably from 1100 to 3400 g/ha, on lawns:

5000 to 25000 g of compound B eg fosetyl-Al+100 to 2000 g/ha of compoundA and more precisely 10000 to 20000 g+250 to 1000 g/ha, i.e. a totaldose of composition according to the invention of from 5100 to 27000g/ha, preferably from 10250 to 21000 g/ha.

The following examples are given purely by way of illustration of theinvention, which they do not limit in any way.

In the figures appended to the present text, the dose of each activematerial, taken in isolation, required for control of thephytopathogenic fungus at the level indicated is compared with that ofthe 2 active materials taken as a mixture. The effective dose of eachactive material taken in isolation is shown on the axis of the abscissaeand of the ordinates and a straight line is traced cutting these 2 axesand connecting these 2 doses. When an active material taken in isolationin not effective, the straight line is parallel to the axis of thecoordinates which shows the doses of this active material. As regardsthe 2 active materials taken as a mixture, the dose of the mixture at agiven ratio in shown by a point.

Example 1

In vivo test of the combination of ICIA5504 with fosetyl-Al with respectto Plasmopara viticola (grape downy mildew) by preventive treatment 72hours before infection.

A suspension comprising the compounds A and B in a liquid mixturecomposed of a surface-active agent (oleate of polyoxyethylenatedderivative of sorbitan) and water is prepared.

The component B is fosetyl-Al; the A/B ratio is 0.05, 0.07 and 0.1 (B/A=20, 15 and 10).

Vine (Vitis vinifera) cuttings, variety Chardonnay, are grown in smallpots. When these seedlings are 2 months old (8- to 10-leaf stage, heightof 10 to 15 cm), they are treated by spraying with the above suspension.

Seedlings, used an controls, are treated with a similar suspension butwhich does not contain active material ("formulation blank").

After 72 hours, each seedling is infected by spraying with an aqueoussuspension of spores of Plasmopara viticola, which suspension isobtained from sporulated leaves infected 7 days previously. These sporesare suspended at a concentration of 100,000 units per cm³ of inoculum.Infection is carried out by spraying the inoculum at the undersurface ofthe leaves.

The infected seedlings are then incubated for seven days at 20-22° C. at90-100% relative humidity under natural light.

Reading is carried out 7 days after infection, in comparison with thecontrol seedlings.

The results obtained are reported in the form of points, correspondingto 50% destruction of the parasite, and are plotted on a Tammes isobolediagram which contains, on the abscissa, the doses of A expressed in ppm(mg/l) and, on the ordinate, the doses of B, also in ppm (mg/l).

The diagram of FIG. 1 is obtained. It appears that the addition offosetyl-Al makes it possible, in an entirely unexpected way, to lowerthe dose of A necessary for the destruction of 50% of the parasite below1.5 ppm (mg/l), which corresponds to the dose of A alone which it isnecessary to apply to obtain the same percentage of destruction.

The arrangement of the points obtained therefore shows an effectdescribed, according to the Tammes method mentioned above, as a"two-sided effect". This arrangement corresponds to a type-III isoboleaccording to the said method (page 75 of the correspondingbibliographical reference already cited) and is characteristic of asynergy. Example 2: In vivo test of the combination of SSF-129 withfosetyl-Al with respect to Plasmopara viticola (grape downy mildew) bypreventive treatment 72 hours before infection.

The same procedure is carried out as in Example 1 but replacing thecompound A (ICIA5504) by SSF-129.

The component B is still fosetyl-Al; the A/B ratio is 0.07, 0.1 and 0.2(B/A =5, 10 and 15).

The diagram of FIG. 2 is obtained. It appears that the addition offosetyl-Al makes it possible, in an entirely unexpected way, to lowerthe dose of A necessary for the destruction of 50% of the parasite below4.6 pmm (mg/l), which corresponds to the dose of A alone which it isnecessary to apply to obtain the same percentage of destruction.

The arrangement of the points obtained therefore shows an effectdescribed, according to the Tammes method mentioned above, as a"two-sided effect". This arrangement corresponds to a type-III isoboleaccording to the said method (page 75 of the correspondingbibliographical reference already cited) and is characteristic of asynergy.

What is claimed is:
 1. A fungicidal composition comprising a synergisticfungicidally effective amount of a compound A which isN-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamideand a compound B which is phosphorous acid, a metal phosphite or analkali metal or alkaline-earth metal salt of phosphorous acid, the A/Bratio by weight being from 0.004 to
 1. 2. A fungicidal compositionaccording to claim 1, wherein the A/B ratio by weight is from 0.0125 to0.4.
 3. A process for the curative or preventative control ofphytopathogenic fungi in plants, said process comprising applying toplants or to the locus in which they grow a synergistic fungicidallyeffective non-phytotoxic amount of a compound A which isN-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamideand a compound B which is phosphorous acid, a metal phosphite or analkali metal or alkaline-earth metal salt of phosphorous acid, the A/Bratio by weight being from 0.004 to
 1. 4. A process according to claim3, wherein the A/B ratio by weight is from 0.0125 to 0.4.
 5. Afungicidal composition comprising a synergistic fungicidally effectiveamount of a compound A which isN-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamideand a compound B which is fosetyl-Al, the A/B ratio by weight being from0.004 to
 1. 6. A fungicidal composition according to claim 5, whereinthe A/B ratio by weight is from 0.0125 to 0.4.
 7. A fungicidalcomposition according to claim 5, wherein the A/B ratio by weight isfrom 0.01 to
 1. 8. A fungicidal composition according to claim 5,wherein the A/B ratio by weight is from 0.033 to 0.4.
 9. A fungicidalcomposition according to claim 5, wherein the A/B ratio by weight isfrom 0.004 to 0.4.
 10. A fungicidal composition according to claim 5,wherein the A/B ratio by weight is from 0.0125 to 0.1.
 11. A fungicidalcomposition according to claim 5, further comprising at least one memberselected from the group consisting of an agriculturally acceptable solidor liquid vehicle and an agriculturally acceptable surface-active agent.12. A fungicidal composition according to claim 11, comprising from0.05% to 95% by weight of compounds A and B.
 13. A process for thecurative or preventative control of phytopathogenic fungi in plants,said process comprising applying to plants or to the locus in which theygrow a synergistic fungicidally effective non-phytotoxic amount of acompound A which isN-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamideand a compound B which is fosetyl-Al, the A/B ratio by weight being from0.004 to
 1. 14. A process according to claim 13, wherein the A/B ratioby weight is from 0.0125 to 0.4.
 15. A process according to claim 13,wherein the synergistic fungicidally effective non-phytotoxic amount ofA and B is applied to crops or lawns to control fungi which arephytopathogenic towards crops or lawns, respectively.
 16. A processaccording to claim 15, wherein the synergistic fungicidally effectivenon-phytotoxic amount of A and B is applied to the aerial parts of theplants.
 17. A process according to claim 15, wherein the synergisticfungicidally effective non-phytotoxic amount of A and B is applied tocrops and wherein the A/B ratio by weight is from 0.01 to
 1. 18. Aprocess according to claim 15, wherein the synergistic fungicidallyeffective non-phytotoxic amount of A and B is applied to crops andwherein the A/B ratio by weight is from 0.033 to 0.4.
 19. A processaccording to claim 15, wherein the synergistic fungicidally effectivenon-phytotoxic amount of A and B is applied to crops at a dose rate offrom 550 to 5500 g/ha.
 20. A process according to claim 15, wherein thesynergistic fungicidally effective non-phytotoxic amount of A and B isapplied to crops at a dose rate of from 1100 to 3400 g/ha.
 21. A processaccording to claim 17, wherein the synergistic fungicidally effectivenon-phytotoxic amount of A and B is applied at a dose rate of from 550to 5500 g/ha.
 22. A process according to claim 17, wherein thesynergistic fungicidally effective non-phytotoxic amount of A and B isapplied at a dose rate of from 1100 to 3400 g/ha.
 23. A processaccording to claim 18, wherein the synergistic fungicidally effectivenon-phytotoxic amount of A and B is applied at a dose rate of from 550to 5500 g/ha.
 24. A process according to claim 18, wherein thesynergistic fungicidally effective non-phytotoxic amount of A and B isapplied at a dose rate of from 1100 to 3400 g/ha.
 25. A processaccording to claim 15, wherein the synergistic fungicidally effectivenon-phytotoxic amount of A and B is applied to lawns and wherein the A/Bratio by weight is from 0.004 to 0.4.
 26. A process according to claim15, wherein the synergistic fungicidally effective non-phytotoxic amountof A and B is applied to lawns and wherein the A/B ratio by weight isfrom 0.0125 to 0.1.
 27. A process according to claim 15, wherein thesynergistic fungicidally effective non-phytotoxic amount of A and B isapplied to lawns at a dose rate of from 5100 to 27000 g/ha.
 28. Aprocess according to claim 15, wherein the synergistic fungicidallyeffective non-phytotoxic amount of A and B is applied to lawns at a doserate of from 10250 to 21000 g/ha.
 29. A process according to claim 25,wherein the synergistic fungicidally effective non-phytotoxic amount ofA and B is applied to lawns at a dose rate of from 5100 to 27000 g/ha.30. A process according to claim 25, wherein the synergisticfungicidally effective non-phytotoxic amount of A and B is applied tolawns at a dose rate of from 10250 to 21000 g/ha.
 31. A processaccording to claim 26, wherein the synergistic fungicidally effectivenon-phytotoxic amount of A and B is applied to lawns at a dose rate offrom 5100 to 27000 g/ha.
 32. A process according to claim 26, whereinthe synergistic fungicidally effective non-phytotoxic amount of A and Bis applied to lawns at a dose rate of from 10250 to 21000 g/ha.